Cindy's Strapon and Fist

A sequel to my previous story, Cindy's Finger (& Her Strap-on)

***

Just as we were finishing dinner, Cindy looked over at me with a sweet and seemingly innocent smile and said, "I really want to fuck you in the ass tonight. You up for it?"

Cindy is nothing if not direct.

I smiled back. "My ass is yours, pretty lady."

"Oh, yeah," she replied.

A month ago I wouldn't have believed that I had come to love being fucked in the ass by my girlfriend with her strap-on. I was too straight, too conventional for that. It all started when Cindy stuck her finger up my ass and I liked it. Amazing where things went from there.

Cindy is bi and we met shortly after she had broken up with a long-term girlfriend. She had just picked up her last box of stuff from her girlfriend's apartment and in the box was a strap-on, which she really wanted to use on me. I considered grabbing my clothes and running but on an impulse said yes. And the rest, as they say, is history, or sodomy, or perhaps a combination of both.

The interesting thing is that when I learned Cindy was bi, I found the fact to be rather sexy, but little more than that. Like most straight men I was turned on by the image of two women making love. I had a passing fantasy about a threesome, but knew better than to make any such suggestion when she was clearly on the rebound from her last girlfriend. I was just glad that she rebounded to me, rather than another woman.

What I hadn't thought anything of was the dynamics of her previous relationship. I only realized after learning up-close and personal about her strap on harness and assortment of dildos that Cindy was, when she chose to be, a top. She liked to dominate.

In the early months of our relationship we had totally convention but also totally hot sex. I tended to take the lead, even if I wasn't always literally on top.

That changed dramatically when she started fucking me with a strap-on. The truth is, I loved it. And no, I didn't beat myself up about "turning gay." I was no more attracted to men than I had been before I took a dildo up the ass. I just understood how pleasurable being on the receiving end of anal sex could be. Gay men and straight men have the same configuration of nerve endings after all. What feels good, feels good.

But, of course, it went beyond nerve endings and sensations. I was no longer solely the top. I was now figuratively and literally the bottom. I was submitting and I was amazed to learn how much I enjoyed the total surrender I felt when Cindy was slamming my ass with a rubber cock. She was in total control and I loved it. The odd and wonderful thing was that my submission didn't so much change our relationship as expand and broaden it, not unlike what her dildos were doing to my asshole.

After dinner, Cindy kissed me and whispered, "let's go take a shower."

The foreplay began as Cindy soaped us both up and rubbed her lovely body against mine, as her hands grabbed my ass. She gave me a particularly wicked smile as she shoved a middle finger up my asshole and said, "I've been looking forward to fucking you all day. I am going to fuck you so hard."

I smiled and moaned happily.

When we rinsed the soap off, she grabbed a large enema bulb which had been sitting on the ledge of the shower. She deftly slid the nozzle into my ass and squeezed the hot soapy water inside me. She followed with a sharp slab to my butt cheek. I yelped and laughed a the same time.

After we dried off I sat on the toilet and Cindy skipped off to the bedroom. Once I was emptied out and took a quick rinse in the shower, I walked into the bedroom where Cindy was lying on her back under the covers. The covers rose in a suspicious mound between her legs. She smiled at me and with a flourish, threw the covers back to reveal her strap on.

I took a quick breath. The dildo in the harness was not the blue realistic rubber cock that she usually plowed me with, but a much larger black dildo she called "black beauty," which she had been threatening to use on me but had never followed through. I guess tonight was the night.

"What do you think?" she asked.

"That is one big cock you have there, pretty lady" I replied.

"Do you think you can handle it?" she asked. Then before I could answer she smiled sweetly and said, "You can handle it."

She then pointed to me and then to the shining black cock. I knew exactly what she wanted. It was part of Cindy's strap-on ritual. Before she fucked me, she always wanted me to suck her dildo. Sometimes she would fuck my face. At first I objected, but Cindy insisted. I was never sure whether to feel humiliation or excitement. Truth is, I felt a mix of both. More than anything else, it completed the role reversal. I decided that as Cindy had no problem sucking my cock, I should return the favor and suck hers.

After becoming used to the size of her smaller life-sized dildo in my throat, I had a hard time even getting my mouth around this large black beast of a cock. I wished my jaws could unhinge. Soon I was gagging, my eyes watering and I had to pull back so that I could breathe.

I heard Cindy laugh. "That's enough. You've done your best. Come here."

I turned from where I was kneeling on the bed. She pulled me closer to her and kissed me passionately.

"Now, let's have some real fun," she whispered in my ear. "Hands and knees."

What in hell am I doing, I asked myself. I got on my hands and knees on the bed.

Cindy was in no hurry. She knelt behind me and started flicking her tongue over and around my asshole, then stuck it in as deep as it would go. I groaned in sybaritic pleasure as she lavished her attention on my ass. Then she danced her tongue up my peritoneum to my balls and then dropped back to my asshole. As far as I was concerned, she could eat my ass forever and for a while it seemed to that was what she was going to do.

Then I felt two fingers slide inside me followed by a cool flood of lube. A third and then a fourth finger slipped in next to the first two and moved slowly in and out. They felt so good. Progressively, the fingers fucking my ass worked their way deeper as they slid in and out. I felt myself being stretched ever wider as the four fingers worked their way toward her knuckles.

Then suddenly the fingers were gone. I was stunned back to the moment by the complete lack of sensation. And then I felt it. The head of her cock, black beauty, was pressing gently against my asshole.

The domed head of the black rubber cock felt huge, far too large to ever fit inside my asshole. I kept my ass high but put my head down on the the pillow and tried to relax, breathing deeply, focusing on accepting the sensations rather than resisting.

At first there was a playful bump, bump, bump of the head of the cock against my ass. Then she began to push, slowly but in earnest. Cindy was determined to fuck my ass with this huge cock and one way or another I was determined to take it. I pushed back against the impossibly large cock pressing against my asshole.

Slowly my sphincter yielded. The pressure was intense as my asshole was stretched wider and wider as the head was buried inside me. The cock head just seemed to get bigger and bigger and bigger until finally, miraculously, it was inside. Now, the shaft of the cock was sliding deeper and deeper.

And then she stopped. "How are you doing?" she asked. I wasn't sure what to say. I was breathing heavily. The feeling was neither pain nor pleasure but a strange amalgam of both. I wasn't sure that I could take it, but I didn't want her to pull out.

"I'm OK," I responded, while not entirely sure that that was true.

She began moving again, fucking me slowly at first, a shallow back and forth that gradually built in speed and depth.

I surrendered to the sensations. I flowed with the steady rhythm of her thrusts until it felt like we were not two people, but separate parts of some strange creation, a living machine where her piston drove forward and back, reaching deep into my very being.

At one point, she slowed as she drew back and squeezed more lube on the shaft. And then she just kept fucking my ass with the huge cock, slower then faster, shallow then and deeper thrusts, testing the limits of the depths of my rectum.

I don't know how long she fucked me but then suddenly she stopped and slowly drew out her "black beauty." I gasped and slumped forward, equal parts happy that it had ended and impossibly sad that it had. I felt the cock resting on my ass cheeks and extending part way up my lower back. Cindy leaned forward and ran her fingers lightly down my back.

"You did very well. I'll be right back. Roll over on you back."

And then she was gone. I slowly rolled over. I knew the position well. I put a pillow under my hips at the edge of the bed and a pillow for my head. My knees were spread and ass was raised slightly and wholly exposed.

What was she going to do to me now? More fucking with "black beauty?" Was that just a warm up?

In a few minutes, she stepped out from the bathroom. She was still wearing the strap-on. The large black dildo swung obscenely like an elephant's trunk as she walked. She was also now wearing black rubber gloves that reached almost to her elbows.

When she reached the bed, she picked up the lube and squirted a healthy serving and started rubbing it onto her gloved right hand and part way up her forearm.

"Are you ready for Round 2?" she asked.

Oh my fucking god, I thought. Can this be really happening? I looked at her lubed arm and realized that it looked no thicker than the shaft of the dildo. Her hand, however, was another matter. Suddenly I felt frightened, while at the same time, strangely excited. My ass felt empty and wanting to be filled. I knew if I said no, she would stop, but somehow I didn't want to stop. Was I crazy?

"Yeah, I'm ready," I replied.

She slathered an ample supply of lube on my ass and began to slide her hand into my asshole. I was already stretched by her big black dildo, so she started with four fingers tucked together, probing in and out, turning and twisting, then pushing deeper. Soon, I felt her tuck her thumb next to the other four, as she probed, pushed and twisted. Soon, she added more lube.

Her hand twisted and probed, pushed deeper then withdrew, then probed deeper again. Lying on my back I watcher her eyes flash and her wicked smile spread across her face as she worked her way inside me. She seemed less like my dear Cindy than some wild animal working to tear me apart.

It felt so good and so bad. The pressure was intense yet not really painful. If I let myself relax and not give in to the fear of what was happening, it felt overpoweringly and strangely wonderful.

Her hand felt far too large, like it would never get inside. But she kept pushing and twisting. The head of the black cock that had so thoroughly fucked me just mimutes before, also felt impossibly large when she first buried it in my ass. If I could take her biggest rubber cock, then surely I could take her hand as well. Or so I told myself.

Finally, she stopped toying with my ass and, with one steady push, began to slide her hand in deeper. I felt the pressure building, higher and higher, with more and more intensely, until I was sure my sphincter couldn't stretch any wider. Then my ass slipped around the widest part of her hand and slid down to her relatively narrow wrist.

I had my eyes closed but opened them when I heard Cindy whisper, almost to herself, "Fuck yeah." Looking down at me she said, "I love the feeling when the ass pulls my hand inside. Amazing."

I didn't say anything, but it was amazing, more than amazing. The feeling of having a woman's hand inside me was completely overwhelming. I felt her move slightly deeper and slowly curl her fingers into a fist.

At first, she was perfectly still, as we both took in the wonder of her clenched hand buried inside me. The feeling was both forceful and intimate. Our bodies were inextricably joined together in the brutal simplicity of her hand reaching inside me. The sensations were similar to a strap on except they seemed totally different. This was no fake rubber cock. This was flesh and blood, my lover's hand and wrist impaling my ass. The most literally connected I had ever been with another person. My heart pounded loudly in my ears and I wondered whether she could feel my heartbeat through her hand.

"How are you doing?" she asked, at slightly more than a whisper.

"Great."

She smiled at me and slowly began to move her hand, in and out, twisting one way and then the other. She fucked me faster and faster and then slowed down to almost a stop only to began moving wildly again.

I moaned and cried out in the pleasure and the sheer intimate madness of it all. "Oh my god," I murmured. "Fuck me, Cindy. Oh, fuck me! Fuck me."

"Oh, fuck yeah," she replied. She drove her hand deeper inside, part way up her forearm and then pulled back like a the piston of some great locomotive. She kept pumping harder and faster as I kept moaning. The lustful fury in her eyes was intoxicating and the feeling as she pounded inside me with her clenched fist was beyond belief. I wasn't sure how much longer I could take it, yet wanted it to go on forever.

And then she slowed to a stop. She stared deeply into my eyes as she began rocking her hand back and forth. I gasped. This was different. Intense but focused. Each time her knuckles rubbed back and forth I felt an electric jolt that was at once very uncomfortable and extremely pleasurable. My cock stiffened.

She laughed. "I have found your prostate gland." She began rocking her hand back and forth faster and faster. I didn't last long. The orgasm seemed to erupt from my very core. Without being touched, my cock began to spurt on my stomach and chest. I cried out in the joy and shock of the mind shattering orgasm that course through my entire body. I lay there shaking.

After few moments to recover, I opened my eyes and saw her staring at me. She looked radiant. I was impaled on the hand of a goddess.

As she watched me closely, she moved her hand and arm deeper, seemingly deeper than she had been before, then slowly pulled back. I felt her clenched fist relax and uncurl as her hand slipped past my sphincter.

I gasped as her hand left me, the last stretch followed by a sense of longing and emptiness. She took off her gloves and softly caressed my face with her right hand.

"Looked like you were having a good time."

I laughed. "Ah, yeah. Indescribable. And you?"

She leaned forward and kissed me deeply, then turned and whispered in my ear. "I do love your ass."

I took a deep breath. "Your fist." I had a difficult time composing my thoughts. "My god. Your fist was fantastic."

She pulled herself up off the bed and unbuckled the strap on. The heavy black dildo fell to the floor with a resounding thud. Then she climbed back up on the bed and straddled my head. She looked at me with an expression that said, "My turn" as she lowered herself onto my face.

I started licking and sucking as she ground herself onto my mouth. She was so wet, her juices flowed across my face. I grabbed her ass with my hands and pulled her ever closer as I licked her clitoris softly then harder. I didn't want to rush things but she was obviously very turned on. Fisting as foreplay. Who could have imagined that?

She was moaning louder and she gasped as I slid two fingers in her ass. I held on tight as she came, hard and loud, riding my face.

Afterwards we held each other for a few minutes, before adjourning again to the shower. Between the lube, sweat, and cum, we were a sticky mess. Close together, we soaped each other up under the warm water, kissing passionately as our bodies rubbed together. Cindy reached for my ass and easily slid in four fingers.

"Shall we begin again?" I asked.

"Don't tempt me," she said with a grin. "Did I mention that I love your ass? Yes, I believe I did."

"I love what you do to my ass." I replied.

"And, baby, I have only begun," she said with her most wicked grin.

Once again, I felt the wonderful confluence of excitement and a bit of fear. I looked forward with glee and dread to learn what she planned to do next. As the water ran over us, I held her body close to mine and didn't want to let go.